WO2009008019A1 - Sels stables de s-adénosylméthionine et procédé de préparation de ceux-ci - Google Patents
Sels stables de s-adénosylméthionine et procédé de préparation de ceux-ci Download PDFInfo
- Publication number
- WO2009008019A1 WO2009008019A1 PCT/IT2007/000736 IT2007000736W WO2009008019A1 WO 2009008019 A1 WO2009008019 A1 WO 2009008019A1 IT 2007000736 W IT2007000736 W IT 2007000736W WO 2009008019 A1 WO2009008019 A1 WO 2009008019A1
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- WIPO (PCT)
- Prior art keywords
- same
- acid
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- salt
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
Definitions
- SAMe S-adenosyknethioni ⁇ e
- SAMe it is intended to indicate both die racemic mixture and die single diastereoisomers (RS)-(+)-S-adenosyl-L-methionine [(RS)-(+)-SAMe)] and (SS)-(+)-
- SAMe corresponds to the following formula:
- SAMe participates in a great number of metabolic processes of fundamental importance for the human body, and its deficiency therefore underlies many organic malfunctions.
- US3893999 describes tri-p-toluensulphonate of SAMe
- US3954726 describes disulphate di-p-toluensulphonate of SAMe
- US4057686 describes a group of SAMe salts which can be indicated overall as SAMe .
- the US patent application No. 20020010147 describes a process for preparing salts of (SS 5 RS)-SAM in which the salified diastereoisomer RS(+) SAMe is present in a much lower amount than, the salified diastereoisomer SS(+) SAMe. It has now been surprisingly found that salts of SAMe having an improved stability over time are obtained by salifying the SAMe with 0.5 — 2.0 moles/mole of a strong inorganic acid with an acid dissociation constant (pKa) of less than 2.5 added with 0.5 — 1.0 moles/mole of an oxide and/ or salt.
- pKa acid dissociation constant
- Said oxide and/ or salt is preferably selected from among calcium oxide, magnesium oxide, calcium chloride, magnesium chloride, calcium sulphate, magnesium sulphate and/ or a mixture thereof.
- Said salts of SAMe according to the present invention preferably contain a high percentage of SAMe. More preferably, the percentage of SAMe in the aforesaid salts is at least 70% by weight, and still more preferably is in the range of 75 - 90%. Salts of SAMe that contain lesser quantities of acid, oxide and/or salt are unacceptable for therapeutic use, since they are subject to degradation phenomena.
- HX is a strong mineral acid having an acid dissociation constant (pKa) of less than 2.5; n and m are independendy in the range of 0.5 - 2.0;
- Y is a calcium oxide, magnesium oxide, calcium chloride, magnesium chloride, calcium iulphate, magnesium sulphate and/or a mixture thereof;
- HX is an acid selected from among hydrochloric acid, sulphuric acid, phosphoric acid, phosphorous _cid, disulphoruc acid and/or 1,4 butanedisulphonic acid.
- S ⁇ Me s.ilrs .lccording to the present invention preferably correspond to the following general formulas (II) and (HII)-
- HX is a strong mineral acid having acid dissociation constant (pKa) of less than 2.5;
- Y is calcium oxide, magnesium oxide, calcium chloride, magnesium chloride, calcium sulphate, magnesium sulphate and/ or a mixture thereof.
- HX is an acid selected from among hydrochloric acid, sulphuric acid, phosphoric acid, phosphorous acid, disulphonic acid and/or 1,4 butanedisulphonic acid.
- the pKa of the aforesaid acids correspond to the following values:
- the improved stability of the salts of SAMe of the present invention is also directly correlated with the size and shape of the product itself in drying phase. This because the shape and size of the final powder influence the lrygroscopicity of the product, which determines the stability of the same to the extent that the closer the hygroscopicity value approaches zero, the greater the stability of the salt of SAMe.
- the particle sizes of the salt according to the present invention are preferably in the range of 20 - 500 ⁇ m, more preferably in the range of 50 - 300 ⁇ m, and the particles are preferably in oval or spherical form, more preferably spherical.
- the drying phase of the product according to the present invention occurs through a lyophilisation passage, preceded by a freezing passage by ultrasonic spray cooling.
- Said freezing is preferably carried out according to the method described in
- the salts of SAMe according to the present invention moreover contain a high percentage of the active diastereoisomer, (SS)-(+)-S-adenosyl-L-methioni ⁇ e, of the
- Said percentage of (SS)-(+)-S-adenosyl-L-methionine is preferably at least 80% by weight, more preferably in the range of 85 - 95% calculated with respect to the sum of the two diastereoisomers.
- a further object of the invention is the use of at least of the salts of formula (I)
- HX is a strong mineral acid having an acid dissociation constant (pKa) of less than 2 5, n and m are independently in the range of 0 5 - 20;
- Y is a calcium oxide, magnesium oxide, calcium chlo ⁇ de, magnesium chloride, calcium sulphate, magnesium sulphate and/or a mixture thereof for the preparation of a medicament for the treatment of depressive states.
- HX is an acid selected from among hydrochloric acid, sulphunc acid, phosphoric acid, phosphorous acid, djsulphoruc acid and/or 1,4 butanedisulphoruc acid
- the salts have a white crystalline aspect with granulometry in the range of 50 - 300 ⁇ m and perfectly spherical form. They are extremely soluble in water up to about 60 mg/mL.
- the high-resolution, thin-layer chromatography shows that the product is free of any impurity.
- Table 1 reports the analytic data of the aforesaid two salts.
- the salts have a white crystalline aspect with granulometry in the range of 50 - 300 ⁇ m and perfectly spherical form. They are extremely soluble in water up to about 60 mg/mL.
- the high-resolution, thin-layer chromatography shows that the product is free of any impurity.
- Table 1 reports the analytic data of the aforesaid two salts.
- the solution was then frozen and lyophilised by spray cooling and subsequently subjected to lyophilisation.
- the salts have a white crystalline aspect with granulometry in the range of 50 - 300 ⁇ m and perfectly spherical form. They are extremely soluble in water up to about 60 mg/mL.
- the high-resolution, thin-layer chromatography shows that the product is free of any impurity.
- Table 1 reports the analytic data of the aforesaid two salts.
- the two salts thus prepared were subjected to quick freezing by spray cooling and subsequent lyophilisation.
- the salts have a white crystalline aspect with granulometry in the range of 50 - 300 ⁇ m and perfectly spherical form. They are extremely soluble in water up to about 60 mg/mL.
- the high-resolution, thin-layer chromatography shows that the product is free of any impurity.
- Table 1 reports the analytic data of the aforesaid two salts.
- the solution was then frozen and lyophilised by spray cooling and subsequently lyophilised.
- the salts have a white crystalline aspect with granulometry in the range of 50 - 300 ⁇ m and perfectly spherical form. They are extremely soluble in water up to about 60 mg/mL.
- the high-resolution, thin-layer chromatography shows that the product is free of any impurity.
- Table 1 reports the analytic data of the aforesaid two salts.
- the solution was frozen and lyophilised by spray cooling and subsequently lyophilised.
- the salts have a white crystalline aspect with granulometry in the range of 50 - 300 ⁇ m and perfectly spherical form. They are extremely soluble in water up to about 60 mg/mL.
- the high-resolution, thin-layer chromatography shows that the product is free of any impurity.
- Table 1 reports the analytic data of the aforesaid two salts.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SI200731645T SI2170920T1 (sl) | 2007-07-10 | 2007-10-22 | Stabilne soli s-adenozilmetionina in postopek za pripravo le-teh |
NZ582149A NZ582149A (en) | 2007-07-10 | 2007-10-22 | Stable salts of s-adenosylmethionine / s-adenosyl-l-methionine and process for the preparation thereof |
CA2707344A CA2707344C (fr) | 2007-07-10 | 2007-10-22 | Sels stables de s-adenosylmethionine et procede de preparation de ceux-ci |
KR1020107000693A KR101455208B1 (ko) | 2007-07-10 | 2007-10-22 | 안정적인 s-아데노실메티오닌의 염 및 이를 제조하기 위한 방법 |
DK07849705.4T DK2170920T3 (en) | 2007-07-10 | 2007-10-22 | STABLE OF SALTS AND S-adenosylmethionine process for its preparation |
EP07849705.4A EP2170920B1 (fr) | 2007-07-10 | 2007-10-22 | Sels stables de s-adénosylméthionine et procédé de préparation de ceux-ci |
AU2007356297A AU2007356297B2 (en) | 2007-07-10 | 2007-10-22 | Stable salts of S-adenosylmethionine and process for the preparation thereof |
RS20150334A RS54021B1 (en) | 2007-07-10 | 2007-10-22 | STABLE S-ADENOSYLMETHIONINE SALTS AND PROCEDURE FOR THEIR PRODUCTION |
BRPI0721887A BRPI0721887B8 (pt) | 2007-07-10 | 2007-10-22 | composto de sal de s-adenosilmetionina e seu uso |
ES07849705.4T ES2536402T3 (es) | 2007-07-10 | 2007-10-22 | Sales estables de S-adenosilmetionina y procedimiento para la preparación de las mismas |
US12/665,808 US8258115B2 (en) | 2007-07-10 | 2007-10-22 | Stable salts of S-adenosylmethionine and process for the preparation thereof |
PL07849705T PL2170920T3 (pl) | 2007-07-10 | 2007-10-22 | Stabilne sole s-adenozylometioniny i sposób ich wytwarzania |
CN2007800536892A CN101730704B (zh) | 2007-07-10 | 2007-10-22 | S-腺苷甲硫氨酸的稳定的盐及其制备方法 |
JP2010515664A JP2010533165A (ja) | 2007-07-10 | 2007-10-22 | S−アデノシルメチオニンの安定な塩およびその調製のための方法 |
NO20100192A NO343103B1 (no) | 2007-07-10 | 2010-02-08 | Stabile salter av S-adenosylmetionin og fremgangsmåter for fremstilling derav |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI2007A001374 | 2007-07-10 | ||
IT001374A ITMI20071374A1 (it) | 2007-07-10 | 2007-07-10 | Sali stabili di s-adenosilmetionina e processo per il loro ottenimento. |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009008019A1 true WO2009008019A1 (fr) | 2009-01-15 |
Family
ID=39639465
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IT2007/000736 WO2009008019A1 (fr) | 2007-07-10 | 2007-10-22 | Sels stables de s-adénosylméthionine et procédé de préparation de ceux-ci |
Country Status (19)
Country | Link |
---|---|
US (1) | US8258115B2 (fr) |
EP (1) | EP2170920B1 (fr) |
JP (2) | JP2010533165A (fr) |
KR (1) | KR101455208B1 (fr) |
CN (1) | CN101730704B (fr) |
AU (1) | AU2007356297B2 (fr) |
BR (1) | BRPI0721887B8 (fr) |
CA (1) | CA2707344C (fr) |
CY (1) | CY1116266T1 (fr) |
DK (1) | DK2170920T3 (fr) |
ES (1) | ES2536402T3 (fr) |
IT (1) | ITMI20071374A1 (fr) |
NO (1) | NO343103B1 (fr) |
NZ (1) | NZ582149A (fr) |
PL (1) | PL2170920T3 (fr) |
PT (1) | PT2170920E (fr) |
RS (1) | RS54021B1 (fr) |
SI (1) | SI2170920T1 (fr) |
WO (1) | WO2009008019A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015028927A1 (fr) * | 2013-08-25 | 2015-03-05 | Mahesh Kandula | Compositions et méthodes de traitement de maladies métaboliques |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014113609A1 (fr) * | 2013-01-16 | 2014-07-24 | Hebert Sam-E Llc | Sels d'indole-3-propionate stables de la s-adénosyl-l-méthionine |
WO2016185413A1 (fr) | 2015-05-20 | 2016-11-24 | Nestec S.A. | Formulations à libération modifiée |
CN106349311B (zh) * | 2016-08-23 | 2018-04-13 | 北京金阳利康医药有限公司 | 从酵母发酵液中提取s‑腺苷蛋氨酸的方法 |
IT201700074957A1 (it) * | 2017-07-04 | 2019-01-04 | Gnosis Spa | Sale di (ss)-adenosil metionina con inositolo esafosfato e procedimento per ottenerlo |
IT202000030914A1 (it) | 2020-12-15 | 2022-06-15 | Mario Antonio Basile | Composizione farmaceutica solida di ademetionina e cannabidiolo e procedimento per ottenerla |
Citations (5)
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US3893999A (en) * | 1972-08-02 | 1975-07-08 | Bioresearch Sas | Salt of S-adenosil-L-methionine and process of preparation |
US4057686A (en) * | 1974-07-12 | 1977-11-08 | Bioresearch Limited | Sulphonic acid salts of S-adenosilmethionine |
US20020010147A1 (en) * | 2000-05-25 | 2002-01-24 | Chementecno S.R.L. | Process for the preparation of pharmaceutically acceptable salts of (SS,RS) -s-adenosyl-l-methionine |
WO2002102823A1 (fr) * | 2001-06-14 | 2002-12-27 | Orchid Chemicals & Pharmaceuticals Limited | Sels stables de s-adenosyl-l-methionine (same) et procede de preparation |
WO2007004244A1 (fr) * | 2005-06-30 | 2007-01-11 | Maria De Luca | Sels ou complexes de donneurs de groupes méthyle avec de l’acide phytique ou ses dérivés et procédé pour leur synthèse |
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IE39517B1 (en) * | 1973-06-27 | 1978-10-25 | Bioresearch Sas | Double salts of s-adenosyl-l-methhionine |
CA1187388A (fr) | 1978-09-20 | 1985-05-21 | American Monitor Corporation | Stabilisation de solutions de reactifs contenant du nadh, du nadph et (ou) des enzymes, et utilisation desdits reactifs pour le dosage des enzymes ou des substrats |
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2007
- 2007-07-10 IT IT001374A patent/ITMI20071374A1/it unknown
- 2007-10-22 CA CA2707344A patent/CA2707344C/fr active Active
- 2007-10-22 RS RS20150334A patent/RS54021B1/en unknown
- 2007-10-22 US US12/665,808 patent/US8258115B2/en active Active
- 2007-10-22 CN CN2007800536892A patent/CN101730704B/zh active Active
- 2007-10-22 AU AU2007356297A patent/AU2007356297B2/en active Active
- 2007-10-22 ES ES07849705.4T patent/ES2536402T3/es active Active
- 2007-10-22 KR KR1020107000693A patent/KR101455208B1/ko active IP Right Review Request
- 2007-10-22 DK DK07849705.4T patent/DK2170920T3/en active
- 2007-10-22 NZ NZ582149A patent/NZ582149A/en unknown
- 2007-10-22 JP JP2010515664A patent/JP2010533165A/ja active Pending
- 2007-10-22 EP EP07849705.4A patent/EP2170920B1/fr active Active
- 2007-10-22 PL PL07849705T patent/PL2170920T3/pl unknown
- 2007-10-22 SI SI200731645T patent/SI2170920T1/sl unknown
- 2007-10-22 PT PT78497054T patent/PT2170920E/pt unknown
- 2007-10-22 BR BRPI0721887A patent/BRPI0721887B8/pt active IP Right Grant
- 2007-10-22 WO PCT/IT2007/000736 patent/WO2009008019A1/fr active Application Filing
-
2010
- 2010-02-08 NO NO20100192A patent/NO343103B1/no unknown
-
2014
- 2014-09-09 JP JP2014183360A patent/JP2015028043A/ja active Pending
-
2015
- 2015-05-13 CY CY20151100420T patent/CY1116266T1/el unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3893999A (en) * | 1972-08-02 | 1975-07-08 | Bioresearch Sas | Salt of S-adenosil-L-methionine and process of preparation |
US4057686A (en) * | 1974-07-12 | 1977-11-08 | Bioresearch Limited | Sulphonic acid salts of S-adenosilmethionine |
US20020010147A1 (en) * | 2000-05-25 | 2002-01-24 | Chementecno S.R.L. | Process for the preparation of pharmaceutically acceptable salts of (SS,RS) -s-adenosyl-l-methionine |
WO2002102823A1 (fr) * | 2001-06-14 | 2002-12-27 | Orchid Chemicals & Pharmaceuticals Limited | Sels stables de s-adenosyl-l-methionine (same) et procede de preparation |
WO2007004244A1 (fr) * | 2005-06-30 | 2007-01-11 | Maria De Luca | Sels ou complexes de donneurs de groupes méthyle avec de l’acide phytique ou ses dérivés et procédé pour leur synthèse |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015028927A1 (fr) * | 2013-08-25 | 2015-03-05 | Mahesh Kandula | Compositions et méthodes de traitement de maladies métaboliques |
Also Published As
Publication number | Publication date |
---|---|
JP2010533165A (ja) | 2010-10-21 |
RS54021B1 (en) | 2015-10-30 |
NO343103B1 (no) | 2018-11-05 |
SI2170920T1 (sl) | 2015-06-30 |
BRPI0721887A2 (pt) | 2014-03-25 |
PL2170920T3 (pl) | 2015-07-31 |
BRPI0721887B1 (pt) | 2019-06-25 |
AU2007356297A1 (en) | 2009-01-15 |
CY1116266T1 (el) | 2017-02-08 |
US20100184715A1 (en) | 2010-07-22 |
NO20100192L (no) | 2010-02-08 |
CA2707344C (fr) | 2014-12-16 |
ITMI20071374A1 (it) | 2009-01-11 |
CN101730704B (zh) | 2013-08-14 |
EP2170920B1 (fr) | 2015-03-11 |
KR101455208B1 (ko) | 2014-10-28 |
PT2170920E (pt) | 2015-07-06 |
NZ582149A (en) | 2012-02-24 |
BRPI0721887B8 (pt) | 2021-05-25 |
CA2707344A1 (fr) | 2009-01-15 |
KR20100032893A (ko) | 2010-03-26 |
US8258115B2 (en) | 2012-09-04 |
ES2536402T3 (es) | 2015-05-25 |
CN101730704A (zh) | 2010-06-09 |
AU2007356297B2 (en) | 2012-05-24 |
EP2170920A1 (fr) | 2010-04-07 |
JP2015028043A (ja) | 2015-02-12 |
DK2170920T3 (en) | 2015-05-11 |
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